A Little League baseball game played in a park in Garden City, N.Y., three days before the Kentucky Derby may have foreshadowed what lay ahead for jockey Javier Castellano on the first Saturday in May. Bottom of the sixth – the last inning – in a 0-0 game, 10-year-old Brady Castellano, Javier’s son, gets his first hit of the season. Steals second. Steals third. Next batter hits a ground ball to second and Castellano beats the throw home, sliding in safely to score the game-winning run. A celebration ensues. “All the parents were going ‘You’re going to win the Kentucky Derby,’ ” Javier Castellano said, recalling the scene. “I said, ‘Pray for me.’ ” Castellano’s prayers for a Kentucky Derby victory were answered on May 6 when he guided 15-1 shot Mage to a one-length victory in the 149th Run for the Roses. The victory capped a lengthy return to glory for Castellano, who had seen his once-bustling business tail off despite a résumé that included four straight Eclipse Awards (2013-16) and a Hall of Fame induction in 2017. In March 2020, Castellano was among the first jockeys to get COVID, and it cost him six weeks of riding. Toward the end of the year, Castellano underwent hip surgery and was out for three months. When he returned in February 2021, he had lost a lot of his regular business. “Mentally, you get frustrated,” Castellano said. “No matter what you did in the past – Hall of Fame, Eclipse Awards – I still didn’t feel like I had the respect, and people they don’t give me the trust and confidence. :: Get ready to bet the Preakness! Join DRF Bets and score a $250 Deposit Match + $10 Free Bet + Free PPs - Promo code: WINNING “But I never give up,” he added. “The good thing with me is I will be persistent, consistently work hard, every single day. It’s going to turn around in a good way. I didn’t give up, and I think that’s the best advice I can give to any athlete, don’t give up. If you’re looking for the dream, you can reach it.” It began to turn around for Castellano last summer at Saratoga. He won three races on opening day and ended the meet with 25 wins. In 2021, he had won 13 races at Saratoga. Castellano’s 27 wins at the 2022 Belmont at Aqueduct fall meet were second only to Irad Ortiz Jr. Earlier this year, Castellano won the George Woolf Award, which honors riders whose careers and personal character earn esteem for the individual and the sport of Thoroughbred racing. The award is voted on by fellow riders. “I was looking for that for many, many years,” said Castellano, 45. “At the beginning of my career, I hoped one day I would win the George Woolf.” And like every rider, Castellano hoped one day he would win the Kentucky Derby. It took longer than expected, as he went winless with his first 15 mounts in the race starting in 2005 with race favorite Bellamy Road finishing seventh. For Castellano, his first Derby victory was worth the wait on several fronts. First, winning the race for trainer Gustavo Delgado held special meaning because both men are natives of Maracaibo, Venezuela, and have a long history together. Castellano’s father rode races for Delgado. As an apprentice, Castellano himself rode a few races for Delgado in Caracas, where Delgado had moved his stable. :: DRF's Preakness Headquarters: Contenders, latest news, and more Castellano relocated to the United States in 1997 at age 19. Delgado didn’t start training in the United States until 2014. In January 2014, when Castellano was honored with his first Eclipse Award for his 2013 season, he invited Delgado to attend the awards ceremony. “I talk with him all the time after he came to United States,” Delgado recalled. “When he won the Eclipse Award, he called me and said ‘You and your family come and sit at my table.’ ” Delgado then put his hand over his heart to display the meaning of that gesture. Another reason the Derby victory was worth the wait for Castellano was because his kids got a chance to enjoy it. Castellano, with his wife, Abby, have three children – Kayla, 17; Sienna, 14; and Brady. “When I was very, very successful in my career my kids were little, they don’t remember those moments,” Castellano said. “Now, thank God, they’re able to enjoy the moment.” “It’s something they’ll never forget and they won’t have to remember it through a photograph,” Abby Castellano said. “They got to experience all the feelings and emotions. I don’t think I would want to change a thing.” When he rides Mage in Saturday’s Preakness, Javier Castellano will be shooting for a third victory in the race, having won it aboard Bernardini in 2006 and Cloud Computing in 2017. After winning the Derby on May 6, Javier Castellano came back a week later and won the Grade 3 Peter Pan on Arcangelo at Belmont Park. It was Castellano’s sixth graded stakes win of 2023, equaling the number he won in all of 2022. When he jumped off Arcangelo, Castellano expressed unabashed, childlike joy, complete with a little shadow boxing. “Feel good,” he said. “Feel like 19 years old.” :: Want to learn more about handicapping and wagering? Check out DRF's Handicapping 101 and Wagering 101 pages.